Allylamine → HCID 18326508, compound

HRID 1250653Notes

Reaction equation

HRID 1250653 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:12][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1.[CH2:19]([NH2:22])[CH:20]=[CH2:21].C(=O)([O-])O.[Na+]>>[CH2:19]([NH:22][C:2]1[N:3]=[C:4]([NH:12][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1)[CH:20]=[CH2:21]

Participants

4

Reactant 3

HCID 7853AllylamineHCID 516892Sodium BicarbonateHCID 18326457HCID 18326457, compound

Product 1

HCID 18326508HCID 18326508, compoundYield 64%

Procedure

339 mg (1.2 mmol) of 2-chloro-7-methyl-4-piperidinoaminothieno[3,2-d]pyrimidine and 1.10 g (19.2 mmol) of allylamine were heated in a sealed tube at 160° C. for 16 hours. After completion of the reaction, the reaction mixture was allowed to resume room temperature, followed by adding a saturated aqueous sodium hydrogen carbonate solution thereto and extraction with ethyl acetate (50 ml×2). After the organic layer was washed with brine and dried over anhydrous sodium sulfate, the solvent was distilled off. The residue was purified by a silica gel chromatography (eluent: ethyl acetate-hexane=1/2) to give 233 mg (yield: 64.0%) of the title compound.

Workup

  1. customAfter completion of the reaction
  2. customto resume room temperature
  3. extractionextraction with ethyl acetate (50 ml×2)
  4. washAfter the organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by a silica gel chromatography (eluent: ethyl acetate-hexane=1/2)

Sources & evidence

ORD record
ord-5220302de2aa4b2c8b4e7ea4999fdee0
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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